Chester Homes under $900,000

Chester Homes under $900,000

Welcome to Chester, a charming town nestled in the heart of the United States, where history meets modern living. Known for its picturesque landscapes and vibrant community, Chester offers a unique blend of small-town charm and urban convenience. With its rich heritage, you can stroll through streets lined with beautifully preserved historic buildings, enjoy local boutiques, and savor the flavors of delightful eateries that reflect the town's diverse culture.

For those seeking a place to call home, Chester presents an array of stunning properties under $900,000, making it an ideal destination for families, young professionals, and retirees alike. These homes showcase a variety of architectural styles, from cozy cottages to spacious modern designs, all set against the backdrop of Chester’s scenic beauty. With an emphasis on quality and comfort, each residence offers a unique opportunity to create lasting memories.

Chester is not just about beautiful homes; it boasts excellent schools, beautiful parks, and a strong sense of community. Residents enjoy a plethora of outdoor activities, from hiking and biking trails to serene picnic spots along the river. Additionally, Chester's strategic location provides easy access to major highways and public transportation, making commuting to nearby cities a breeze.

Whether you’re looking to settle down or invest in a vibrant community, Chester's real estate market is brimming with opportunities. Discover your dream home today and experience the warmth and charm that this delightful town has to offer!

Newest Chester Homes under $900,000

223 Evelyne St, Chester
$799,000
3 Beds ⋅ 3 Baths
Profressional Photos COMING SOON! Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and gathering. Two additional bedrooms and a full bathroom are located upstairs. A standout feature is the expanded family room over the garage, known as the FROG. The oversized garage option provides additional space for parking and storage below and a larger recreation room above—perfect for a media room, game room, or additional living space. Plumbing is already in place within the wall for a potential future full bathroom, offering added flexibility to make the space your own. Gibson’s Grant offers a waterfront community setting with an outdoor pool, clubhouse, fitness center, and fishing and crabbing pier. Enjoy direct access to the Cross Island Trail and easy access to Route 50, the Bay Bridge, waterfront restaurants, shopping, and everyday conveniences. Discover the space, versatility, and coastal lifestyle that make this home a special opportunity on Kent Island.

223 Evelyne St, Chester

Listing courtesy of Samson Properties. Contact:

2011 Stevens Dr, Chester
$489,900
3 Beds ⋅ 2 Baths
Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

2011 Stevens Dr, Chester

Listing courtesy of Samson Properties. Contact:

111 Marshgrass Way Unit 43, Chester
$744,900
2 Beds ⋅ 3 Baths
Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, gas fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing.  Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

111 Marshgrass Way Unit 43, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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